Pyridine → HCID 69663720, compound

HRID 396351Notes

Reaction equation

HRID 396351 reaction equation
S(O)(=O)(=O)C.[O:6]1[CH2:10][CH2:9][NH:8][C:7]1=[O:11].[H][H].[N:14]1C=CC=CC=1.C(OC(=O)C)(=O)C>CN(C=O)C.[Pd].O.C1COCC1>[C:10]([NH2:14])(=[O:6])[CH3:9].[O:6]1[CH2:10][CH2:9][NH:8][C:7]1=[O:11]

Participants

9

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 20145393HCID 20145393, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69663720HCID 69663720, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above azide (from Example 6)(21.67 g, 61.16 mmol) dissolved in DMF (400 mL) and THF (500 mL) was degassed with nitrogen for 30 minutes whereupon 10% Pd/C (4.74 g, 4.4 mmols) was added and the reaction hydrogenated on a Parr apparatus (60 psi of hydrogen) for 14 hr. The reaction mixture was removed from the Parr apparatus and placed under a nitrogen atmosphere whereupon pyridine (5.44 mL, 67.3 mmols) and acetic anhydride (6.35 mL, 67.3 mmols) were added. After stirring for 1 hr the reaction mixture was filtered through a pad of Celite, washing thoroughly with methanol and then copious amounts of 50% MeOH/CH2Cl2 (ca. 2 L). The filtrate was evaporated to afford the crude acetamide in DMF. The mixture was slowly added to water (2 L) and the ppt collected on a filter, washed with water (5×400 mL) and dried in a vac oven (50° C.) to provide the acetamide as an analytically pure white solid (14.2 g, 63% yield). The combined filtrates were extracted with methylene chloride (5×200 mL), dried over Na2SO4 and concentrated. Water was added to the residue and the resulting ppt was filtered off and dried in a vac oven (50° C.) to afford a second crop of the acetamide as a light tan, fluffy solid (5.61 g, 25%). For the analytically pure material Mp=229-230° C., decomp. MS (M+1)=371 m/z.

Workup

  1. additionwas added
  2. customThe reaction mixture was removed from the Parr apparatus
  3. additionwere added
  4. filtrationwas filtered through a pad of Celite
  5. washwashing thoroughly with methanol
  6. customThe filtrate was evaporated
  7. customto afford the crude acetamide in DMF
  8. customthe ppt collected on a filter
  9. washwashed with water (5×400 mL)
  10. customdried in a vac oven (50° C.)

Sources & evidence

ORD record
ord-674eea9376cd4a2d94222e503c80a3dd
Source dataset
uspto-grants-2003_08
Patent number
US06608081B2

Reaction notes

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